Structural characterization and Hirshfeld surface analysis of 2-iodo-4-(penta­fluoro-λ6-sulfan­yl)benzo­nitrile.

Autor: Espiet, Jean C. González, Cruz, Juan A. Cintrón, Cruz, Dalice M. Piñero
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Zdroj: Acta Crystallographica Section E: Crystallographic Communications; Feb2020, Vol. 76 Issue 2, preceding p231-234, 8p
Abstrakt: The title compound, C7H3F5INS, a penta­fluoro­sulfanyl (SF5) containing arene, was synthesized from 4-(penta­fluoro­sulfan­yl)benzo­nitrile and lithium tetra­methyl­piperidide following a variation to the standard approach, which features simple and mild conditions that allow direct access to tri-substituted SF5 inter­mediates that have not been demonstrated using previous methods. The mol­ecule displays a planar geometry with the benzene ring in the same plane as its three substituents. It lies on a mirror plane perpendicular to [010] with the iodo, cyano, and the sulfur and axial fluorine atoms of the penta­fluoro­sulfanyl substituent in the plane of the mol­ecule. The equatorial F atoms have symmetry-related counterparts generated by the mirror plane. The penta­fluoro­sulfanyl group exhibits a staggered fashion relative to the ring and the two hydrogen atoms ortho to the substituent. S-F bond lengths of the penta­fluoro­sulfanyl group are unequal: the equatorial bond facing the iodo moiety has a longer distance [1.572(3)Å] and wider angle compared to that facing the side of the mol­ecules with two hydrogen atoms [1.561(4)Å]. As expected, the axial S-F bond is the longest [1.582(5)Å]. In the crystal, in-plane C-H...F and N...I inter­actions as well as out-of-plane F...C inter­actions are observed. According to the Hirshfeld analysis, the principal inter­molecular contacts for the title compound are F...H (29.4%), F...I (15.8%), F...N (11.4%), F...F (6.0%), N...I (5.6%) and F...C (4.5%). [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index